Perchloric Acid → HCID 21437984, compound

HRID 2397373Notes

Reaction equation

HRID 2397373 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=1)([O-])=O.Cl(O)(=O)(=O)=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 21437958HCID 21437958, compound

Product 1

HCID 21437984HCID 21437984, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6 gm (0.02 mol) of 4-(2'-nitro-4-biphenylyl)-4-oxo-butyric acid were hydrogenated in 60 ml of acetic acid and 2.5 ml of perchloric acid in the presence of 2.5 gm of palladium/barium sulfate (5%) as catalyst at room temperature and at a pressure of 5 atmospheres in a Parr-autoclave. After absorption of the calculated quantity of hydrogen, the catalyst was vacuum-filtered off, and the solvent was removed in vacuo. The residue was dissolved in water and admixed with ether. By addition of sodium bicarbonate solution, the aqueous phase was adjusted to a pH-value of about 5. Now, the ether solution was separated, washed with water and the solvent was removed. The obtained 4-(2'-amino-4-biphenylyl)-butyric acid was dissolved in ether and mixed with cyclohexylamine; the precipitated cyclohexylamine salt was collected and recrystallized from methylene chloride and then from acetone/ether. Melting point 123°-126° C.

Workup

  1. customat room temperature
  2. customAfter absorption of the calculated quantity of hydrogen
  3. filtrationthe catalyst was vacuum-filtered off
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in water
  6. additionBy addition of sodium bicarbonate solution
  7. customNow, the ether solution was separated
  8. washwashed with water
  9. customthe solvent was removed
  10. dissolutionThe obtained 4-(2'-amino-4-biphenylyl)-butyric acid was dissolved in ether
  11. additionmixed with cyclohexylamine
  12. customthe precipitated cyclohexylamine salt was collected
  13. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-f5d2b99ef9914e94b998314221c6dcf6
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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